FI76561C - Foerbaettrat foerfarande foer framstaellning av enkainid. - Google Patents
Foerbaettrat foerfarande foer framstaellning av enkainid. Download PDFInfo
- Publication number
- FI76561C FI76561C FI824234A FI824234A FI76561C FI 76561 C FI76561 C FI 76561C FI 824234 A FI824234 A FI 824234A FI 824234 A FI824234 A FI 824234A FI 76561 C FI76561 C FI 76561C
- Authority
- FI
- Finland
- Prior art keywords
- hydrogen
- methyl
- equivalents
- pyridylacetyl
- hydrogenation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title claims description 5
- PJWPNDMDCLXCOM-UHFFFAOYSA-N encainide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=CC=C1CCC1N(C)CCCC1 PJWPNDMDCLXCOM-UHFFFAOYSA-N 0.000 title description 13
- 229960001142 encainide Drugs 0.000 title description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 238000005984 hydrogenation reaction Methods 0.000 claims description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229910052697 platinum Inorganic materials 0.000 claims description 12
- CZDIHHFANHXHCA-UHFFFAOYSA-N 4-methoxy-n-phenyl-2-(2-pyridin-2-ylacetyl)benzamide Chemical compound C=1C=CC=NC=1CC(=O)C1=CC(OC)=CC=C1C(=O)NC1=CC=CC=C1 CZDIHHFANHXHCA-UHFFFAOYSA-N 0.000 claims description 10
- 229960000583 acetic acid Drugs 0.000 claims description 9
- 239000012362 glacial acetic acid Substances 0.000 claims description 6
- BEBIQSRTLZBRRT-UHFFFAOYSA-N lithium;2-methylidenepyridin-1-ide Chemical compound [Li+].[CH2-]C1=CC=CC=N1 BEBIQSRTLZBRRT-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- IHMUJQKXSXXRSK-UHFFFAOYSA-N methyl 2-[(4-methoxybenzoyl)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)C1=CC=C(OC)C=C1 IHMUJQKXSXXRSK-UHFFFAOYSA-N 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 12
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- -1 2- (4-methoxybenzamido) phenyl Chemical group 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 229940102398 methyl anthranilate Drugs 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 4
- 229940043279 diisopropylamine Drugs 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000003416 antiarrhythmic agent Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PPQUTVKWIUCDQP-UHFFFAOYSA-N 4-methoxy-n-phenyl-2-(2-pyridin-2-ylacetyl)benzamide;hydrochloride Chemical compound Cl.C=1C=CC=NC=1CC(=O)C1=CC(OC)=CC=C1C(=O)NC1=CC=CC=C1 PPQUTVKWIUCDQP-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 238000001311 chemical methods and process Methods 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DBDVAKGHPZJLTH-UHFFFAOYSA-N 1-(2-phenylethyl)piperidine Chemical class C1CCCCN1CCC1=CC=CC=C1 DBDVAKGHPZJLTH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/330,298 US4394507A (en) | 1981-12-14 | 1981-12-14 | Process for production of encainide |
| US33029881 | 1981-12-14 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI824234A0 FI824234A0 (fi) | 1982-12-09 |
| FI824234L FI824234L (fi) | 1983-06-15 |
| FI76561B FI76561B (fi) | 1988-07-29 |
| FI76561C true FI76561C (fi) | 1988-11-10 |
Family
ID=23289147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI824234A FI76561C (fi) | 1981-12-14 | 1982-12-09 | Foerbaettrat foerfarande foer framstaellning av enkainid. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4394507A (de) |
| JP (1) | JPS6058231B2 (de) |
| KR (1) | KR890000419B1 (de) |
| AT (1) | AT378182B (de) |
| CA (1) | CA1213282A (de) |
| CH (1) | CH655101A5 (de) |
| DK (1) | DK156648C (de) |
| ES (2) | ES8405767A1 (de) |
| FI (1) | FI76561C (de) |
| GR (1) | GR77107B (de) |
| HU (1) | HU186190B (de) |
| IT (1) | IT1149399B (de) |
| NL (1) | NL8204775A (de) |
| PT (1) | PT75980B (de) |
| SE (1) | SE454442B (de) |
| YU (1) | YU44035B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4800226A (en) * | 1986-02-25 | 1989-01-24 | Bristol-Myers Company | Process intermediate for the preparation of encainide |
| US4675409A (en) * | 1986-02-25 | 1987-06-23 | Bristol-Myers Company | Process for the preparation of encainide |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2317303A (en) * | 1940-12-07 | 1943-04-20 | Merck & Co Inc | Heterocyclic nitrogen containing compounds, and processes for making the same |
| US4064254A (en) * | 1971-03-03 | 1977-12-20 | Mead Johnson & Company | Substituted piperidines therapeutic process and compositions |
| US3931195A (en) * | 1971-03-03 | 1976-01-06 | Mead Johnson & Company | Substituted piperidines |
| CA961038A (en) * | 1971-03-03 | 1975-01-14 | Joseph L. Minielli | Substituted piperidines |
| US4000143A (en) * | 1971-03-03 | 1976-12-28 | Mead Johnson & Company | Substituted piperidines |
| SE7607114L (sv) * | 1976-06-22 | 1977-12-23 | Bofors Ab | Sett att framstella hydrokloriden av n-metylpiperidin-2-karbonsyra-2,6-xyllidid |
-
1981
- 1981-12-14 US US06/330,298 patent/US4394507A/en not_active Expired - Fee Related
-
1982
- 1982-11-18 GR GR69848A patent/GR77107B/el unknown
- 1982-11-22 CA CA000416079A patent/CA1213282A/en not_active Expired
- 1982-11-25 KR KR8205318A patent/KR890000419B1/ko not_active Expired
- 1982-12-02 IT IT49608/82A patent/IT1149399B/it active
- 1982-12-07 ES ES517996A patent/ES8405767A1/es not_active Expired
- 1982-12-07 YU YU2710/82A patent/YU44035B/xx unknown
- 1982-12-09 NL NL8204775A patent/NL8204775A/nl unknown
- 1982-12-09 JP JP57214747A patent/JPS6058231B2/ja not_active Expired
- 1982-12-09 FI FI824234A patent/FI76561C/fi not_active IP Right Cessation
- 1982-12-10 DK DK551582A patent/DK156648C/da not_active IP Right Cessation
- 1982-12-13 HU HU824018A patent/HU186190B/hu not_active IP Right Cessation
- 1982-12-13 CH CH7245/82A patent/CH655101A5/de not_active IP Right Cessation
- 1982-12-13 SE SE8207112A patent/SE454442B/sv not_active IP Right Cessation
- 1982-12-13 PT PT75980A patent/PT75980B/pt not_active IP Right Cessation
- 1982-12-14 AT AT0454082A patent/AT378182B/de not_active IP Right Cessation
-
1984
- 1984-03-01 ES ES530218A patent/ES530218A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CH655101A5 (de) | 1986-03-27 |
| NL8204775A (nl) | 1983-07-01 |
| SE8207112L (sv) | 1983-06-15 |
| DK156648C (da) | 1990-03-05 |
| ES517996A0 (es) | 1984-06-16 |
| SE454442B (sv) | 1988-05-02 |
| PT75980B (en) | 1985-12-20 |
| YU271082A (en) | 1985-03-20 |
| IT1149399B (it) | 1986-12-03 |
| ES8506274A1 (es) | 1985-07-01 |
| FI824234A0 (fi) | 1982-12-09 |
| KR840002355A (ko) | 1984-06-25 |
| JPS6058231B2 (ja) | 1985-12-19 |
| ATA454082A (de) | 1984-11-15 |
| CA1213282A (en) | 1986-10-28 |
| DK551582A (da) | 1983-06-15 |
| FI76561B (fi) | 1988-07-29 |
| PT75980A (en) | 1983-01-01 |
| JPS58105963A (ja) | 1983-06-24 |
| US4394507A (en) | 1983-07-19 |
| YU44035B (en) | 1990-02-28 |
| GR77107B (de) | 1984-09-06 |
| SE8207112D0 (sv) | 1982-12-13 |
| HU186190B (en) | 1985-06-28 |
| ES530218A0 (es) | 1985-07-01 |
| KR890000419B1 (ko) | 1989-03-17 |
| ES8405767A1 (es) | 1984-06-16 |
| FI824234L (fi) | 1983-06-15 |
| IT8249608A0 (it) | 1982-12-02 |
| DK156648B (da) | 1989-09-18 |
| AT378182B (de) | 1985-06-25 |
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